Cargando…
Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp(3))−H bond arylation via photoredox/nickel d...
Autores principales: | , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Nature Publishing Group UK
2019
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6685991/ https://www.ncbi.nlm.nih.gov/pubmed/31391466 http://dx.doi.org/10.1038/s41467-019-11392-6 |
_version_ | 1783442474884136960 |
---|---|
author | Cheng, Xiaokai Lu, Huangzhe Lu, Zhan |
author_facet | Cheng, Xiaokai Lu, Huangzhe Lu, Zhan |
author_sort | Cheng, Xiaokai |
collection | PubMed |
description | The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp(3))−H bond arylation via photoredox/nickel dual catalysis. Sterically hindered chiral biimidazoline ligands are designed for this asymmetric cross-coupling reaction. Readily available alkyl benzenes and aryl bromides with various functional groups tolerance can be easily and directly transferred to useful chiral 1,1-diaryl alkanes including pharmaceutical intermediates and bioactive molecules. This reaction proceeds smoothly under mild conditions without the use of external redox reagents. |
format | Online Article Text |
id | pubmed-6685991 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
spelling | pubmed-66859912019-08-09 Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis Cheng, Xiaokai Lu, Huangzhe Lu, Zhan Nat Commun Article The asymmetric cross-coupling reaction is developed as a straightforward strategy toward 1,1-diaryl alkanes, which are a key skeleton in a series of natural products and bioactive molecules in recent years. Here we report an enantioselective benzylic C(sp(3))−H bond arylation via photoredox/nickel dual catalysis. Sterically hindered chiral biimidazoline ligands are designed for this asymmetric cross-coupling reaction. Readily available alkyl benzenes and aryl bromides with various functional groups tolerance can be easily and directly transferred to useful chiral 1,1-diaryl alkanes including pharmaceutical intermediates and bioactive molecules. This reaction proceeds smoothly under mild conditions without the use of external redox reagents. Nature Publishing Group UK 2019-08-07 /pmc/articles/PMC6685991/ /pubmed/31391466 http://dx.doi.org/10.1038/s41467-019-11392-6 Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/. |
spellingShingle | Article Cheng, Xiaokai Lu, Huangzhe Lu, Zhan Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis |
title | Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis |
title_full | Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis |
title_fullStr | Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis |
title_full_unstemmed | Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis |
title_short | Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis |
title_sort | enantioselective benzylic c–h arylation via photoredox and nickel dual catalysis |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6685991/ https://www.ncbi.nlm.nih.gov/pubmed/31391466 http://dx.doi.org/10.1038/s41467-019-11392-6 |
work_keys_str_mv | AT chengxiaokai enantioselectivebenzyliccharylationviaphotoredoxandnickeldualcatalysis AT luhuangzhe enantioselectivebenzyliccharylationviaphotoredoxandnickeldualcatalysis AT luzhan enantioselectivebenzyliccharylationviaphotoredoxandnickeldualcatalysis |